A biomimetic strategy for the synthesis of the tricyclic dibenzofuran-1,4-dione core of popolohuanone E.

@article{Anderson2005ABS,
  title={A biomimetic strategy for the synthesis of the tricyclic dibenzofuran-1,4-dione core of popolohuanone E.},
  author={James C. Anderson and Ross M. Denton and Claire Wilson},
  journal={Organic letters},
  year={2005},
  volume={7 1},
  pages={
          123-5
        }
}
A concise synthesis of the complete tricyclic dibenzofuran-1,4-dione aromatic core of popolohuanone E has been demonstrated by mild base treatment of a biquinone intermediate, thus establishing a biomimetic route to this family of heterocyclic ring systems and the total synthesis of popolohuanone E. 
A concise synthetic approach to parvistemin A and (±)-diperezone
A concise synthetic approach to symmetric biquinone skeletons has been developed through a new biomimetic oxidative phenolic coupling of 1,2,4-trihydroxyarenes using K3[Fe(CN)6] or FeCl3 as the
Synthesis of parvistemin A via biomimetic oxidative dimerization.
The first synthesis of the naturally occurring benzoquinone dimer parvistemin A is reported. The key step is the late stage iron(III) mediated dimerization of a 1,2,4-trihydroxyarene to give the
General Methodologies Toward cis-Fused Quinone Sesquiterpenoids. Enantiospecific Synthesis of the epi-Ilimaquinone Core Featuring Sc-Catalyzed Ring Expansion
TLDR
The utility of Sc(OTf)3 as a mild catalyst for formal 1C insertion in complex settings is demonstrated and a stereocontrolled approach to the cis-decalin framework of clerodane diterpenes and biologically active quinone sesquiter penes is reported.
Total Synthesis of Selaginpulvilin C and D Relying on in Situ Formation of Arynes and Their Hydrogenation.
The total syntheses of selaginpulvilins C and D is described. The key strategy for the construction of the core fluorene moiety involves in situ formation of an aryne intermediate followed by its
Facile Synthesis of Quinone Dimer Derivatives Substituted with Sulfanyl Groups and Their Properties
Quinone dimers are readily prepared quantitatively from 2-sulfanyl-1,4-dimethoxybenzene by oxidative treatment. The oxidative coupling progressed in a highly regioselective manner. Removal of O-pro...
Accessing Polyoxygenated Dibenzofurans via the Union of Phenols and o-Benzoquinones: Rapid Syntheses of Metabolites Isolated from Ribes takare.
The construction of polyoxygenated dibenzo[b,d]furan frameworks from the union of substituted phenols/naphthols and o-benzoquinones via a Michael-oxidation-oxa-Michael cascade is reported. The power
Asymmetric aza-[2,3]-Wittig sigmatropic rearrangements: chiral auxiliary control and formal asymmetric synthesis of (2S, 3R, 4R)-4-hydroxy-3-methylproline and (-)-kainic acid.
A survey of 16 different chiral auxiliaries and a variety of strategies found that an (-)-8-phenylmenthol ester of a glycine derived migrating group can control the absolute stereochemistry of
...
1
2
3
...

References

SHOWING 1-10 OF 17 REFERENCES
Studies toward the Total Synthesis of Popolohuanone E: Enantioselective Synthesis of 8-O-MethylpopolohuanoneE
8-O-Methylpopolohuanone E (2) was synthesized in a highly convergent manner starting from the cis-fused decalin derivative accessible from the (−)-Wieland−Miescher ketone analogue. The synthetic
A strategy for the synthesis of popolohuanone E: formal total synthesis of (±)-arenarol
TLDR
A strategy for the synthesis of popolohuanone E, an oxidatively dimerised arenarol derivative with selective cytotoxic behaviour against non-small cell human lung cancer cells, is described, along with preliminary model studies concerning the formation of the homo-biaryl nucleus.
A mild deprotection strategy for allyl-protecting groups and its implications in sequence specific dendrimer synthesis.
TLDR
The utility of the current methodology in sequence specific dendrimer synthesis is demonstrated and the mild deprotection strategy for allyl ethers under basic conditions in the presence of a palladium catalyst is described.
A biomimetic approach to dihydrobenzofuran synthesis.
A method for an acid-catalyzed construction of dihydrobenzofuran heterocycles (14) from 2-(2'-hydroxyethyl)quinone precursors 10 is presented. The putative oxonium ion intermediate 17 formed by an
...
1
2
...